Deleting Applications with DM

Trying to delete some applications on my 9930, (vietnamese char, yahoo messenger, etc.) using DM. In the Applications window I check all the boxes for apps I want to delete (they turn into a red 'X'), then I hit the 'Apply' button on the bottom right of the screen. DM runs it through a backup process, then an 'update of applications' process, then a 'retrieving wirelessly delivered application modules', then the phone shuts down & reboots on it's own, but a window pops up and says 'Blackberry Desktop Software cannot communicate to the connected device, please hit Retry to attempt to connect to the device'. This has happened 3x's, and after each reboot, and reconnection with DM, the same application list appears as before I attempted to delete the files! Any ideas on why? Am I running an outdated version of DM?